CNN's S.E. Cupp on Her Offscreen Relationship With Trump: "We Liked Each Other"

"In a very dysfunctional business, CNN happens to be the most functional network I’ve worked at," the commentator says.

This is the latest in an ongoing series of one-on-ones with the political pundits who have been at the forefront of the cable-news conversations this election season.

Like a lot of TV pundits, S.E. Cupp has been the target of derisive tweets from Donald Trump. He’s called her “one of the dumber pundits” on TV and “a totally biased loser who doesn’t have a clue.” But the incoming fire was all the more pointed because Cupp had a casual professional relationship with Trump prior to his campaign. She first met him several years ago when they were both appearing on Fox News Channel; at the time, he was peddling the false birther conspiracy about President Obama.

A few years later, in 2011, Trump asked Cupp to introduce him at the annual Faith and Freedom Conference. She knows many people in Trump’s inner circle and has become acquainted with his sons Don Jr. and Eric, with whom she shares a love of hunting. “He’s never grabbed my genitalia,” quips Cupp. “And so I was looking forward to his campaign. But obviously he took it to a dark place pretty early on. I knew I wasn’t going to be supporting him. It’s just for me personally a very bizarre culmination of events.”

Age: 37Current residence: Washington, D.C.Education: Cornell University (BA), New York University (MA)Political persuasion: Log Cabin RepublicanPolitical experience: She’s come by punditry via writing, penning two books — Why You’re Wrong About the Right, with Brett Joshpe, and Losing Our Religion: The Liberal Media’s Attack on Christianity. Her writing has appeared in Politico, The Washington Post, Daily Caller and The American Spectator.Network: political commentator, CNN; columnist, New York Daily NewsViral moment: Trump’s call for a “total and complete shutdown of Muslims entering the United States” in the wake of ISIS-coordinated attacks in Paris and the shooting in San Bernardino perpetrated by a Muslim couple who became radicalized sent the pundit sphere into overdrive and produced a memorable tussle between Cupp and Trump spokesperson Katrina Pierson, with Cupp admonishing: “Peddling this unconstitutional, un-American, un-conservative garbage has got to stop.” After schooling Pierson on all the reasons Trump could never legally enact such a ban, including the Immigration and Nationality Act of 1965, Pierson seemed to suggest that the laws should not apply to Muslims. “So what? They’re Muslim,” said Pierson. An exasperated Cupp exclaimed: “So what?! That’s not the America we live in, Katrina!”

You’ve appeared across the political media spectrum, from Glenn Beck’s digital network to MSNBC, before joining CNN exclusively in 2013. In your view, which network has the best handle on this crazy election?

I’ll say, in a very dysfunctional business, CNN happens to be the most functional network I’ve worked at. Beyond that I don’t know that I want to get into picking the others apart because you just never know where you’re going to land.

How do you prep for an appearance?

It’s just staying on top of it 24/7. The phone’s never far away. The TV’s always on. We are constantly on the news cycle; either watching the news, making the news, talking about the news. You don’t have to prep if you’ve been covering this for years. Maybe you want to look at the most recent polling or you want to pull up a data set on early voting in Ohio, but when you cover politics day-to-day and you’ve been doing it for many election cycles, you’re prepared. You either know this stuff because you’ve been doing it so long or you don’t and that shows real quick. The prep is following all the stories. And not just the stories, but what people are saying about the stories because that inevitably becomes the next beat.

One of your CNN colleagues, Ana Navarro, made headlines when she repeatedly repeated the word “pussy” in talking about the Access Hollywood tape that caught Trump in an extremely lewd and misogynistic conversation.

I get to do Bill Maher’s [HBO program Real Time] about twice a year and that’s always great. Bill is fun. He keeps me on my toes. I really enjoy that. But on a regular basis, Van Jones is my jam. I would show up anywhere to talk about anything with Van. And I’m lucky enough, not only to do that on television for CNN, but traveling to do left-right debates at colleges or for groups or work associations. He’s not only brilliant, but also one of very few people who want to have meaningful conversations that progress to a solution. We have a deep respect for one another. It doesn’t feel like work when we’re on together. So any minute with Van is just a total pleasure.

How do you deal with the haters on social media?

It’s been flipped on its head this year because I’m not supporting my own party’s nominee. In fact, I’m openly critical of him. So the social media attacks I get are not from the left, they’re from the alt-right and that’s a particular level of gross. Think like Holocaust pictures and photos of lynchings directed at you. On the other hand, I can’t go five minutes without someone on Twitter saying, "I’m a Democrat and I think you’re great!" Which does not help my brand. I appreciate it, I really do, but it’s been weird. These are things you just have to roll with and keep doing what you think is right and noble and good.

What’s it like these days when you run into Trump?

It’s surreal. I’ve been saying awful things about him, which are all true and still there’s this moment of recognition that we’re all here just doing the job.